Iodine-mediated ring-closing iodoamination with concomitant N-debenzylation for the asymmetric synthesis of polyhydroxylated pyrrolidines

Stephen G. Davies, Rebecca L. Nicholson, Paul D. Price, Paul M. Roberts, Angela J. Russell, Edward D. Savory, Andrew D. Smith, James E. Thomson

Research output: Contribution to journalArticlepeer-review

59 Citations (Scopus)

Abstract

Treatment of a range of homochiral unsaturated beta-amino esters (containing a cis-dioxolane unit) with iodine promotes a novel ring-closing alkene iodoamination reaction which proceeds with concomitant N-debenzylation, providing a simple and stereoselective route to iodomethyl pyrrolidines. Functional group interconversion of the resulting iodomethyl pyrrolidines upon treatment with AgOAc proceeds via the corresponding aziridinium ion, with Subsequent deprotection giving access to polyhydroxylated pyrrolidines. (C) 2009 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)758-772
Number of pages15
JournalTetrahedron: Asymmetry
Volume20
Issue number6-8
DOIs
Publication statusPublished - 7 May 2009

Keywords

  • JASPINE-B PACHASTRISSAMINE
  • HOMOCHIRAL LITHIUM AMIDES
  • D-LYXO-PHYTOSPHINGOSINE
  • CONJUGATE ADDITION
  • (2S,3R)-3-AMINO-2-HYDROXYDECANOIC ACID
  • STEREOSELECTIVE-SYNTHESIS
  • GLYCOSIDASE INHIBITORS
  • ORGANIC-SYNTHESIS
  • AMINO-ACIDS
  • ROUTE

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